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Nemorubicin CAS: 108852-90-0

Category: Inhibitors
Product Name: Nemorubicin
Cat No: I000374
CAS No: 108852-90-0
Synonyms: (7S,9S)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7-[(2R,4S,5S,6S)-5-hydroxy-4-[(2S)-2-methoxymorpholin-4-yl]-6-methyloxan-2-yl]oxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
Molecular Formula: C32H37NO13
Molecular Weight: 643.64
SMILES: O=C1C2=C(O)C(C[C@](C(CO)=O)(O)C[C@@H]3O[C@H]4C[C@H](N5C[C@@H](OC)OCC5)[C@H](O)[C@H](C)O4)=C3C(O)=C2C(C6=C1C=CC=C6OC)=O
InChI: InChI=1S/C32H37NO13/c1-14-27(36)17(33-7-8-44-22(12-33)43-3)9-21(45-14)46-19-11-32(41,20(35)13-34)10-16-24(19)31(40)26-25(29(16)38)28(37)15-5-4-6-18(42-2)23(15)30(26)39/h4-6,14,17,19,21-22,27,34,36,38,40-41H,7-13H2,1-3H3/t14-,17-,19-,21-,22-,27+,32-/m0/s1
InChIKey: CTMCWCONSULRHO-UHQPFXKFSA-N
Solubility: DMSO: ≥ 47 mg/mL
Target: Microtubule/Tubulin
IC50: 80 nM [1]
Storage: Store at -20°C
CAS 108852-90-0,Nemorubicin
  • Description

Nemorubicin(Methoxymorpholinyl doxorubicin; MMDX; PNU 152243) is a 3'-deamino-3'[2-(S)-methoxy-4-morpholinyl]derivative of doxorubicin, Nemorubici has the anticancer activity on human hepatocellular carcinoma with an IC50 of 80 nM.
IC50 value: 80 nM [1]
Target: anticancer
in vitro: Methoxymorpholinyl doxorubicin (PNU 152243) is a morpholinyl analog possessing a methoxymorpholinyl group at the 3' position of the sugar moiety, which, compared with doxorubicin, appears to be less cardiotoxic and more cytotoxic against multidrug-resistant tumor cells. In this study, we report the anticancer activity of PNU 152243 on human hepatocellular carcinoma (HCC) in vitro and in vivo. The average IC50 value of PNU was 0.08 microM [1]. Microsome-activated MMDX exhibited nanomolar IC(50) values in growth-inhibition assays of human tumor cell lines representing multiple tissues of origin: lung (A549 cells), brain (U251 cells), colon (LS180 cells), and breast (MCF-7 cells).MMDX cytotoxicity was substantially increased in Chinese hamster ovary cells after stable expression of CYP3A4 in combination with P450 reductase [2].
in vivo: In vivo antitumor activity experiments revealed that TAO completely suppressed the ability of 90 microg/kg MMDX i.v., a dose close to the LD10, to delay growth of s.c. M5076 tumors in C57BL/6 mice and to prolong survival of DBA/2 mice with disseminated L1210 leukemia. Moreover, TAO administration markedly inhibited the therapeutic efficacy of 90 microg/kg MMDX i.v. in mice bearing experimental M5076 liver metastases; a complete loss of MMDX activity was observed in liver metastases-bearing animals receiving 40 microg/kg MMDX i.v. plus TAO [3].

  • Spec

Appearance:white solid powder
Purity: > 98%

  • References


1:Virtual Cross-Linking of the Active Nemorubicin Metabolite PNU-159682 to Double-Stranded DNA. Scalabrin M, Quintieri L, Palumbo M, Riccardi Sirtori F, Gatto B.Chem Res Toxicol. 2017 Feb 20;30(2):614-624. doi: 10.1021/acs.chemrestox.6b00362. Epub 2017 Jan 25. PMID: 28068470
2:Nemorubicin and doxorubicin bind the G-quadruplex sequences of the human telomeres and of the c-MYC promoter element Pu22. Scaglioni L, Mondelli R, Artali R, Sirtori FR, Mazzini S.Biochim Biophys Acta. 2016 Jun;1860(6):1129-38. doi: 10.1016/j.bbagen.2016.02.011. Epub 2016 Feb 23. PMID: 26922833
3:The interaction of nemorubicin metabolite PNU-159682 with DNA fragments d(CGTACG)(2), d(CGATCG)(2) and d(CGCGCG)(2) shows a strong but reversible binding to G:C base pairs. Mazzini S, Scaglioni L, Mondelli R, Caruso M, Sirtori FR.Bioorg Med Chem. 2012 Dec 15;20(24):6979-88. doi: 10.1016/j.bmc.2012.10.033. Epub 2012 Nov 3. PMID: 23154079
4:In vitro hepatic conversion of the anticancer agent nemorubicin to its active metabolite PNU-159682 in mice, rats and dogs: a comparison with human liver microsomes. Quintieri L, Fantin M, Palatini P, De Martin S, Rosato A, Caruso M, Geroni C, Floreani M.Biochem Pharmacol. 2008 Sep 15;76(6):784-95. doi: 10.1016/j.bcp.2008.07.003. Epub 2008 Jul 11. PMID: 18671948
5:Nemorubicin. Broggini M.Top Curr Chem. 2008;283:191-206. doi: 10.1007/128_2007_6. PMID: 23605633
6:Formation and antitumor activity of PNU-159682, a major metabolite of nemorubicin in human liver microsomes. Quintieri L, Geroni C, Fantin M, Battaglia R, Rosato A, Speed W, Zanovello P, Floreani M.Clin Cancer Res. 2005 Feb 15;11(4):1608-17. PMID: 15746066 Free Article
7:LC-MS-MS determination of nemorubicin (methoxymorpholinyldoxorubicin, PNU-152243A) and its 13-OH metabolite (PNU-155051A) in human plasma. Fraier D, Frigerio E, Brianceschi G, James CA.J Pharm Biomed Anal. 2002 Oct 15;30(3):377-89. PMID: 12367663


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